Simple rhodium–chlorophosphine pre-catalysts for the ortho-arylation of phenols

Bedford, Robin B.; Betham, Michael; Caffyn, Andrew J. M.; Charmant, Jonathan P. H.; Lewis‐Alleyne, Lesley C.; Long, Philip D.; Polo-Cerón, Dorian; Prashar, Sanjiv

doi:10.1039/b718128k

Cited by 93 publications

(51 citation statements)

References 12 publications

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“…[128] Thus, almost the same results were obtained with a combination of commercially available [RhCl(cod) 2 ] and iPr 2 PCl (Table 44). [128] Thus, almost the same results were obtained with a combination of commercially available [RhCl(cod) 2 ] and iPr 2 PCl (Table 44).…”

Section: Directed Reactionssupporting

confidence: 65%

Removable Directing Groups in Organic Synthesis and Catalysis

2011

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Directing groups have been widely used in recent years to achieve control over all aspects of reaction selectivity in a wide range of transformations involving transition-metal catalysis and organometallic reagents. In cases when the existing functional group within a substrate is unsuited to achieve efficient intramolecular delivery of a reagent or catalyst, the specific introduction of an appropriately designed removable reagent-directing group can be a solution to this problem. In this Review we give an overview of the state of the art in this area, including the stoichiometric and catalytic use of directing groups.

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Section: Directed Reactionssupporting

confidence: 65%

Removable Directing Groups in Organic Synthesis and Catalysis

2011

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“…[206] Among a variety of different chlorophosphine preligands investigated, iPr 2 PCl (299) gave rise to most efficient catalysis and also enabled a significant reduction in the catalyst loading (Scheme 113). However, a satisfactory efficiency was only obtained with ortho-substituted phenols.…”

Section: Rhodium-catalyzed Direct Arylationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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The area of transition-metal-catalyzed direct arylation through cleavage of C-H bonds has undergone rapid development in recent years, and is becoming an increasingly viable alternative to traditional cross-coupling reactions with organometallic reagents. In particular, palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations. Furthermore, less expensive copper, iron, and nickel complexes were recently shown to be effective for economically attractive direct arylations.

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“…[206] Unter [211] der einen erweiterten Anwendungsbereich aufwies und z. B. die effiziente C-H-Funktionalisierung mit Arylbromiden ermög-lichte (Schema 118).…”

Section: Rhodiumkatalysierte Direkte Arylierungenunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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Das Gebiet der übergangsmetallkatalysierten direkten Arylierung unter C‐H‐Bindungsbruch hat in den letzten Jahren eine rasante Entwicklung erfahren, was dazu führte, dass sich solche Methoden immer mehr als Alternativen zu den herkömmlichen Kreuzkupplungen mit metallorganischen Reagentien etabliert haben. Insbesondere wurden zahlreiche Palladium‐ und Rutheniumkatalysatoren beschrieben, welche die direkte Arylierung von (Hetero)arenen mit anspruchsvollen Reaktionspartnern ermöglichen; hierzu gehören elektrophile Arylchloride und ‐tosylate oder auch einfache Arene in gekreuzten dehydrierenden Arylierungen.

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Simple rhodium–chlorophosphine pre-catalysts for the ortho-arylation of phenols

Abstract: Simple chlorodiisopropylphosphine adducts of rhodium, either pre-formed or formed in situ, prove to be highly effective catalysts for the ortho-arylation of phenols.

Cited by 93 publications

References 12 publications

Removable Directing Groups in Organic Synthesis and Catalysis

Removable Directing Groups in Organic Synthesis and Catalysis

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

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